Rational resolution of the isosteric enantiomers of 6,11-dihydrodibenzo[b,e]thiepin-11-ol and conversion to the two isosteric diastereoisomers of the calcium channel blocker UK-74,756

摘要

Sulfoxidation of the (+)-Noe-lactol derivative of racemic 6,11-dihydrodibenzo[h,e]thiepin-11-ol broke the isosterism and converted an inseparable mixture of two compounds into a separable mixture of four. X-Ray structural determination on one oi these and subsequent manipulation provided resolved 6,11-dihydrodibenzo[b,e]thiepin-11-ol auld all four sulfoxides in known configurations, and enabled the resolution by synthesis of the two isosteric diastereoisomers of the calcium channel blocker UK-74,756. (C) 2001 Elsevier Science Ltd. All rights reserved. [References: 19]